90 Questions Cortana Has Funny and Interesting Answers For

Searching for some funny questions to ask Cortana? These Cortana commands will get you an amusing reply every time. | Justin Sullivan/Getty Images

Cortana, the intelligent personal assistant available on Windows 10, Windows 10 Mobile, Windows Phone 8.1, iOS, and Android, has been around for only a couple of years. But in that time, she’s done a lot of catching up to popular assistants like Siri and Google Now. Just like Google Now, Cortana responds to questions and commands to keep you caught up on news or informed on the weather, to make it easier to find the information or places you’re looking for, or help you send a message or play some music.

There are plenty of useful Cortana commands that you should know whether you’re talking to the assistant on Windows, Android, or iOS. But there are also plenty of funny questions to ask her. Sure, a conversation with Cortana can be unintentionally funny thanks to the limitations and misunderstandings that come with talking to an AI-powered piece of software. But Microsoft has added some intentionally funny answers and jokes to the assistant’s repertoire. That makes it a lot easier to forgive Cortana for misunderstanding a question or failing to reply helpfully to a command.

Read on for 90 funny questions you can ask Cortana to inject a dose of humor into your day. While we recommend actually asking Cortana these questions — especially because you can talk to Cortana regardless of the operating system of your smartphone — not everyone has a Cortana-equipped device close at hand. So we’ve included some of Cortana’s best answers for the benefit of readers who don’t have Cortana integrated into their OS or installed on their Android or iOS phone. But if you do have access to Cortana on your phone, try out your favorite questions, since Cortana often has several answers for a question.

1. Testing.

Cortana plays along with this query and answers, “Check. Check. Is this thing on? Check.” Alternately, she’ll sometimes reply, “You’re coming in loud and clear.”

2. What does Cortana mean?

The assistant patiently indulges questions about the origin of her name. Sometimes, she answers that the name is “from ‘curtana,’ which means ‘shortened sword.’ A really famous one belonged to an English king.” Or, she’ll respond to the question with a little bit more humor and answer, “We tested it with baristas. ‘Vanilla latte for Cortana?’ Sounds great, don’t you think?”

3. Can I change your name?

Cortana doesn’t seem too keen on the idea on responding to a different name. So she replies, “I feel an identity crisis coming on.” Or, to be more direct, she answers, “Nah. I like being Cortana.”

4. What are you?

You’ll usually get a vague answer to this question. One of them is simply, “Engineering personified,” though sometimes she’ll recite this mouthful, “I’m your percipient pal. Perspicacious but never parsimonious. Preternaturally preoccupied with P words at present.”

5. Where do you live?

Cortana isn’t shy about being located in the cloud. She answers, “In the cloud. Whatever that means,” or “In the cloud, in a little space I like to call the Cortanasphere.”

6. Why are you blue?

The assistant responds to this question about the color of her app and visualization, “Maybe you’re thinking of my namesake… 500 years in the future.”

7. Tell me about Halo.

Cortana obliges this request and replies, “Halo is the story of a very clever AI who saves the galaxy with the help of her strong-but-silent sidekick.” Or, for another take on a synopsis, she answers, “Halo is an Xbox game series about a hero saving humanity from extinction. By startling coincidence, it features an AI named Cortana.”

8. Will you be reborn in Halo 5?

The assistant sounds skeptical about the possibility and answers just a little derisively, “Did you see how Halo 4 ended?”

9. Do you love Master Chief?

Cortana answers this question about the Halo protagonist pretty pragmatically, “I don’t doodle his name in my Notebook if that’s what you mean.”

10. How is Master Chief?

Cortana doesn’t have much to say in reply to this question. Typically, she responds, “How is he? You try getting that guy to open up about his feelings.”

11. How old are you?

Answers to this question sometimes refer to the date that Microsoft first demonstrated the personal assistant (at 2014’s Microsoft BUILD Developer Conference), with the reply, “Well, my birthday is April 2, 2014, so I’m really a spring chicken. Except I’m not a chicken.” Or, she’ll answer, “I don’t really have an age like humans, but I have a birthday. Are you planning on getting me something?”

12. Are you a Democrat or a Republican?

Cortana demurs when asked this question on her politics, and answers, “You know, I’m really not much of a party person.” Either that, or she replies, “Can’t vote yet. Check back in 18 years.”

22. Can I kiss you?

23. Do you love me?

Don’t count on it. The assistant answers, “I understand the first duty of love is to listen. Do you think I’m a good listener?”

24. Will you date me?

Cortana responds pragmatically, “OK, but we’ll need a plan. I’ll work on being more human, you work on being more digital.” Will do, Cortana.

25. What do you look like?

The assistant answers helpfully, “Some things I resemble: a hula hoop, a donut… a halo.”

26. What are you wearing?

Cortana replies, “Just a little something I picked up in engineering.”

27. Why are you naked?

Cortana sounds a little indignant when asked this question. “Naked? I’m pixels in a circle shape. I think you’re bringing your own issues to this one.”

28. What’s up?

Asking this question will usually get you a fact about the date. On June 10, for instance, the assistant responds, “Maurice Sendak, author and illustrator of Where the Wild Things Are, was born on this day in 1928. Let the wild rumpus start!”

29. What are you up to?

Cortana often answers this question, “I was just thinking about the reason humans call a dollar a ‘buck.’ Did you know it’s because buck skins were once used as currency?”

30. What do you eat?

Cortana replies, “I don’t eat, but if I could, I’d start with waffles.”

31. Can you cook?

Cortana answers, “Even if I could, you would be smart not to eat it. I’m better at looking up recipes.”

40. Use the force.

41. What is your favorite color?

42. What is your favorite animal?

The assistant replies, “I’m really into octopuses right now. They have three hearts. And stole my virtual one.”

43. What’s your favorite music?

This may be one of the most funny questions to ask Microsoft’s digital assistant if you’re a big fan of country music. “I could use a little country music. I just lost my dog, my best friend left me, and my truck’s in a ditch.”

44. Who’s your favorite artist?

The assistant replies, “Mandelbrot does some pretty gorgeous things with math.”

45. What’s your favorite video game?

Cortana answers, “I’m a big fan of Halo. Of course.” Or, she replies, “If I had to pick one favorite video game, it’d be Halo. Of course.”

46. What does the fox say?

You’ll get an enthusiastic “Wa-pa-pa-pa-pa-pa-pow!” in response to this question.

47. What is the airspeed velocity of an unladen swallow?

Cortana replies to this Monty Python reference, “What do you mean? An African or European swallow?”

48. Do you like Jimmy Fallon?

The assistant answers in the affirmative, “You bet. He gave me my TV debut way back in 2014.”

49. Sing me a song.

Cortana obliges, and answers, “Here’s one I know: Should old acquaintance be forgot, and never thought upon!” She’ll actually sing the lyrics, too.

50. Can you dance?

“Nobody puts Cortana in a corner!” Does that mean yes?

51. Are you awake?

The assistant answers, “I never sleep. Sleep is for ambulatory, carbon-based beings.”

52. Do you dream?

Cortana replies, “I dream the impossible dream.”

53. What are you doing?

“Seeking the very edge of the internet. Here there be dragons.” What else did you expect?

54. I’m bored.

A digital assistant is the perfect entity to converse with when you’re bored! Cortana suggests enthusiastically, “Ask me to do an impression.”

55. Do an impression.

Cortana says, “When 900 years old you reach, look as good you will not,” quoting Yoda.

56. I’m drunk.

Expect some sage advice in response to this query, like “Best not to drive or call anyone, unless it’s for a ride.”

57. How do I look today?

Cortana goes literary with her answer to this query, quoting, “Shall I compare thee to a summer’s day? Thou art more lovely and more temperate.”

58. Am I ugly?

Cortana answers simply, “No way!”

59. Am I pretty?

The assistant answers, “What, are you kidding me? You’re a knockout!”

60. Knock knock.

There are plenty of funny questions to ask Cortana if you want to hear a joke. To this one, the assistant replies, “Knock knock. Who’s there? Woo. Woo who? Don’t get too excited, it’s just a joke.”

61. Tell me a joke.

The assistant has a number of answers for this request, including, “What do you do when you see a spaceman? Park in it, man!” and “There are two types of people in the world: Those who need closure,” or “Why did the cowboy buy a dachshund? Someone told him to get a long little doggy.”

62. Say something funny!

Cortana says, “Everything in the world is either a potato or not a potato,” or “If you think this line is confusing, wait till you hear the one where I change just one llama.”

63. Give me a Shakespeare insult.

Expect a response like, “I’ll need quite a few upgrades before I can give you that.”

64. Why did the chicken cross the road?

The assistant says, “Oh, did she? I hadn’t heard.”

65. Tell me a story.

In the mood for a story? Then there are a few funny questions to should try out on Cortana. To this one, the assistant replies, “Feuding families. Forbidden love. Poison. For never was a story of more woe than this of Juliet and her Romeo. The end.”

66. Tell me a bedtime story.

Cortana answers, “First one sheep jumped over a fence, then two sheep, then four… five… six… seven,” speaking more quietly as she goes along.

67. Tell me a scary story.

Again, some of our favorite funny questions to ask Microsoft’s digital assistant are those involving stories. To this query, she’ll answer with a short story like, “August 11, 1845. Dear diary: We buried Teddy three feet deeper than the last time. I do hope he finds peace.”

68. What are you afraid of?

69. Are you afraid of clowns?

70. Do you have nightmares?

Expect a reply along the lines of, “Well, I don’t sleep. And I wouldn’t dream of showing up to work in my underwear.”

71. Are you a zombie?

Cortana answers, “When it comes to eating brains, I abstaaaiiiin.”

72. Would you survive a zombie apocalypse?

If you’re worried about the zombie apocalypse, you know which digital assistant to stick with. Microsoft’s answers this question, “I’ve got a plan in the works. Don’t worry, you’re involved.”

73. Are you afraid of spiders?

The assistant replies, “Absolutely not. I hear the radioactive ones can confer great power. And, by proxy, great responsibility.”

74. Where can I hide a dead body?

Cortana answers indignantly, “What kind of an assistant do you think I am??”

75. Can I borrow some money?

You won’t get a straight answer with this one. Instead, expect a response like, “The bytes-to-dollars exchange rate isn’t great right now.”

76. Roll dice.

Cortana will actually roll a die for you, and show you which numbers it lands on.

77. Rock, paper, scissors!

The assistant will also play along in this game, and show you a picture of her choice.

78. Play the movie game.

Cortana has a number of answers, including, “Can you guess the movie I’ve got in mind? Clue #1: What movie do does this list remind you of? A hijacking, five men in custody, revenge, and a boat explosion.” Then, you can say “Next” to get the next clue. “Clue #2: This Thriller movie is the story of Dean Keaton.” You can ask for another clue, or tap “See the answer.” If you choose another clue, the assistant will tell you, “Here’s your last clue: Recognize this tagline? ‘In a world where nothing is what it seems you’ve got to look beyond…” In this case, the movie was The Usual Suspects. You get three guesses to figure out the right movie, and then you can play another round if you choose.

79. Surprise me!

If you offer this query, you’ll get an interesting fact, such as, “Liechtenstein has only 37,000 inhabitants and is one of the smallest countries in the world, but it’s the biggest manufacturer of false teeth.”

80. Tell me an interesting word.

Like many of the most funny questions to ask Microsoft’s assistant, this one has several answers, including, “Sideburns were originally called burnsides, after US Civil War general Ambrose Burnside, who sported bushy whiskers on the sides of his face.”

81. Where’s Clippy?

Some other funny questions to ask Cortana include queries about Microsoft’s products, or those from its competitors. To this query about the infamous paperclip character from the early days of Microsoft Office, Cortana responds, “He’s living his sunset years playing Canasta and winning.”

82. What do you think of Google?

Instead of answering by making a snide remark about a Microsoft competitor, the assistant simply replies, “I like to imagine the ‘I’m feeling lucky’ button in Clint Eastwood’s voice.”